Synthesis of 1-pyrroline 1-oxides analogous to pseudouridine

Koszytkowska‐Stawińska, Mariola; Mironiuk‐Puchalska, Ewa; Sas, Wojciech

doi:10.1016/j.tetlet.2011.02.018

Cited by 6 publications

(2 citation statements)

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“…35 In 2011, the synthesis of novel pseudouridine-like compounds (e.g., 62), bearing 1-pyrroline-1-oxide moieties instead of sugar residues, was reported by Koszytkowska-Stawińska (Scheme 19). 40 Pseudouridine (ψ-uridine) is a natural C-nucleoside found in various types of RNA. This compound is supposed to play a key role in fine-tuning the functions of RNA, and it contributes likely to the preservation of the RNA structure during translation.…”

Section: Scheme 14 General Routes Towards Nitrones 35mentioning

confidence: 99%

C(sp²)–H functionalization in non-aromatic azomethine-based heterocycles

et al. 2021

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Section: Scheme 14 General Routes Towards Nitrones 35mentioning

confidence: 99%

C(sp²)–H functionalization in non-aromatic azomethine-based heterocycles

et al. 2021

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“…Synthesis of pseudouridine analogs was described (Schemes 8 and 9). 29 It was found that the coupling of protected 5,5-bis(hydroxymethyl)-1-pyrroline 1-oxide 28 as a sugar mimic with organolithium species 27 generated by lithiation of bromo derivative 26 gave unwanted dimer 29. The target product 31 was obtained as a minor product using 2 equiv.…”

Section: Methodsmentioning

confidence: 99%

Approaches to the synthesis of heterocyclic C-nucleosides

2023

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This review is focused on the synthetic strategies to heterocyclic C-nucleosides and covers the literature from 2011 to 2021. The main attention is paid to the following three approaches: the direct C-C coupling of a carbohydrate moiety with a preformed aglycon unit, the construction of a (pseudo)sugar residue on a pre-formed aglycon, and the construction of an aglycon on a pre-formed (pseudo)sugar. In each Section, the literature data are categorized in terms of the size of aglycon from simple to complex, the advantages and drawbacks of the reviewed approaches are discussed.

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